Visible-Light-Promoted C(sp3)–H Bond Functionalization toward Aminothiazole Skeletons from Active Methylene Ketones and Thioureas DOI
Haichang Guo, Lei Wang, Renhua Zheng

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(13), P. 2091 - 2098

Published: Feb. 14, 2023

Abstract A novel and efficient visible-light-induced method is developed for the one-pot synthesis of functionalized 2-aminothiazoles from easily accessible active methylene ketone derivatives different thioureas at room temperature. The mild reaction conditions, green chemistry, straightforward work-up, high yields products make this procedure useful construction 2-aminothiazole derivatives.

Language: Английский

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

Citations

63

Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes DOI
Zhongyi Zhang,

Zhong‐Wei Hou,

Hao Chen

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3543 - 3548

Published: Jan. 1, 2023

An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes with 2-bromoethan-1-ol as the brominating reagent has been developed.

Language: Английский

Citations

50

Radical relay cyclization/C–C bond formation of allyloxy-tethered aryl iodides with quinoxalin-2(1H)-ones via polysulfide anion photocatalysis DOI
Zhongyi Zhang, Yaqin Zhou, Jiehui Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(8), P. 1708 - 1713

Published: Jan. 1, 2024

A visible-light-induced radical relay cyclization/C-C bond formation of quinoxalin-2(1

Language: Английский

Citations

26

Paired electrochemical C–H bromination of (hetero)arenes with 2-bromoethan-1-ol DOI

Yanxia Lv,

Zhong‐Wei Hou,

Pinhua Li

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 990 - 995

Published: Jan. 1, 2023

A site-selective electrochemical C–H bromination of (hetero)arenes with 2-bromoethan-1-ol by releasing available ethylene oxide and hydrogen through paired electrolysis has been developed.

Language: Английский

Citations

35

Electrochemical Dearomatizing Spirocyclization of Alkynes with Dimethyl 2-Benzylmalonates to Spiro[4.5]deca-trienones DOI
Laiqiang Li,

Zhong‐Wei Hou,

Pinhua Li

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(13), P. 8697 - 8708

Published: June 9, 2022

An electrochemical dearomatizing spirocyclization of alkynes with dimethyl 2-benzylmalonates for the preparation spiro[4.5]deca-trienones has been developed. This approach adopts ferrocene (Cp2Fe) as an electrocatalyst to produce carbon-centered radical intermediates from C–H-based malonates, which obviates forthputting noble-metal reagents, sacrificial chemical oxidants and 2-bromomalonates. A wide variety spiro compounds are efficiently prepared satisfactory results under mild conditions.

Language: Английский

Citations

33

A Straightforward Approach to Fluorinated Pyrimido[1,2-b]indazole Derivatives via Metal/Additive-Free Annulation with Enaminones, 3-Aminoindazoles, and Selectfluor DOI

Zhaoliang Xu,

Xiao Geng,

Yiwen Cai

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(10), P. 6562 - 6572

Published: April 29, 2022

A novel and efficient three-component reaction with two C–N bonds one C–F bond formation has been reported, which provides a straightforward route to variety of fluorinated pyrimido[1,2-b]indazole derivatives. This transformation the advantage excellent functional group compatibility, including aliphatic aromatic substituents enaminones. Moreover, metal additives are not necessary for this reaction, is great significance synthesis application heterocycles.

Language: Английский

Citations

30

Photocatalytic C–H Thiocyanation of NH2-Enaminones and the Tunable Synthetic Routes to 2-Aminothiazoles and 2-Thiazolinones DOI

Junlong Zeng,

Jie‐Ping Wan, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 13195 - 13203

Published: Sept. 15, 2022

Visible light photocatalytic reactions of NH2-enaminones and ammonium thiocyanate for chemoselective α-C-H thiocyanation have been realized the first time, providing a sustainable route synthesis thiocyanated NH2-enaminones. In addition, enaminone products can be flexibly transformed into 2-aminothiazoles 2-thiazolinones via simple operation.

Language: Английский

Citations

30

Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1H)-ones with Acyloxy Nitroso Compounds DOI

Runye Gao,

Fang Wang, Xiao Geng

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(39), P. 7118 - 7122

Published: Sept. 25, 2022

Herein, a photoinitiated radical relay reaction of quinoxalin-2(1H)-ones, with acyloxy nitroso compounds as source radicals, is described. Although the C-H functionalization quinoxalin-2(1H)-ones has been investigated, its difunctionalization, simultaneous construction C-C and N-N bonds directly via reaction, rarely reported. Moreover, obtained products underwent sequential reactions to access C7-NO2 under mild conditions.

Language: Английский

Citations

25

Photoinduced Three‐Component Cyclization of Arylamines, Enaminones and Difluorobromoacetates to 2,3‐Difunctionalized Quinolines DOI
Jie Huo, Xiao Geng, Wanmei Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(20), P. 3539 - 3543

Published: Aug. 26, 2022

Abstract A photoinduced multicomponent reaction of arylamines, enaminones and difluorobromoacetates for the synthesis 2,3‐difunctionalized quinolines is reported. This strategy features broad functional groups tolerance wide substrate scopes that enables further synthetic applications obtained products. Mechanistic studies reveal intermolecular [3+3] cyclization between in‐situ generated 1,3‐vinylimine ions arylamines key step in this transformation. magnified image

Language: Английский

Citations

23

I2-mediated coupling of quinazolinone enamines with 2-aminopyridines: a new strategy to access spiroquinazolinones DOI

Jingxi Fang,

Zhentao Pan, Tong Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(11), P. 2355 - 2360

Published: Jan. 1, 2023

Herein, we report a novel, rapid and efficient route to the spiroquinazolinone framework via an umpolung strategy mediated by molecular iodine. A library of functionalized iodide salts was synthesized in moderate good yields under ambient, metal-free mild conditions. The current methodology opens up new concise for construction spiroquinazolinones.

Language: Английский

Citations

14